Potassium Hydroxide → (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetic acid

HRID 653298Notes

Reaction equation

HRID 653298 reaction equation
C[O:2][C:3](=[O:20])/[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:19])[CH2:17][Cl:18])[S:13][CH:14]=1)=[N:5]\[O:6][CH2:7][CH2:8][CH3:9].[OH-].[K+]>C(O)C.O>[Cl:18][CH2:17][C:16]([NH:15][C:12]1[S:13][CH:14]=[C:10](/[C:4](=[N:5]/[O:6][CH2:7][CH2:8][CH3:9])/[C:3]([OH:20])=[O:2])[N:11]=1)=[O:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14230755methyl (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetate

Product 1

HCID 14230754(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.2 g of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid methyl ester in 50 ml of ethanol is added under ice-cooling and stirring a solution of 2.23 g of potassium hydroxide (85%) in 20 ml of water, and the mixture is stirred for 5 hours at room temperature, followed by concentration under reduced pressure. The concentrate is dissolved in 30 ml of water, and washed twice with 30 ml each portion of ethyl acetate, followed by addition of activated charcoal. The charcoal is removed by filtration and the filtrate is then adjusted to pH 2 with 1N--HCl, and the resulting crystals are collected by filtration, washed with water, hexane and ether in this order to yield 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid, m.p. 170°-171° C.(decomp.).

Workup

  1. temperaturecooling
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe concentrate is dissolved in 30 ml of water
  4. washwashed twice with 30 ml each portion of ethyl acetate
  5. additionfollowed by addition of activated charcoal
  6. customThe charcoal is removed by filtration
  7. filtrationHCl, and the resulting crystals are collected by filtration
  8. washwashed with water, hexane and ether in this order

Sources & evidence

ORD record
ord-55c4fa8994a74a6a9d9fe47f5b9d6ccc
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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